Dyes of the anthraquinone series.



UNITED sirAT as PATENT OFFICE.

HERMANN FRIEDMANN, 0F ELBERFELD; GERMANY, ASSIGNOB TO FARBEN'FABRIKEN VORM. FRIEDR. BAYER & CO., OE ELBERFELD, GERMANY, A CORPORATION OF Specification of Letters Patent. Patented June'24 1913-.

GERMANY.

. DYES OF THE ANTHRAQUINONE SERIES.

No Drawing.

NHR are A +HNo,=A V Nlh v u (ortho) (R meaning H, alkyl, aryl, etc.) The azimino compounds are from yellow to blue to green compounds soluble in con- Application filed January 13. 1913 Serial No. 741,730..

ingagents they are converted into sulf onic acids dyeing wool. The halogenized prodquinones, valuable vat dyes being obtained. In order to illustrate the new process more fully the following example is-given, the

tolyla mino-2 amino- 3 bromoanthraquinone are dissolved in 50 parts of glacial acetic acid (60 Be.) Then a solution of 2 parts of sodium nitrite in 6 parts of water is added at 01 0 C. After a short time the ,red solufiltered off and recrystallized. from .niftro' benzene? Thus long yellow needles aredb;- tained, which-are dissolved by concentrated yellow color. The reaction probably in centrated sulfuric acid generally with a yel- The dyestufl dyes' cotton in the hydro i sulfite vat yellow shades. The sulfonic acid (obtained bysulfonating) dyes wool an acid bath in yellow shades.

Analogous azimids are obtained -from other ortho-diaminoanthraquinones, such as 1.2- ,or 2.3-diaminoanthraquinone ortfrom derivatives which are still substituted by auxochromic groups or such ones which are capable of entering into reaction. The 1.5-

v-di-para-tolylaminoQXS-diamino 3 7 dibromoanthraquinone c. 9. yields a brown, the 1.2-diamino t-paratolylaminoanthraquinone and the 1.2.5.6 tetramine-4.8-di-para-tolylaminoanthraquinone yields blue to green colaccordance with the following equation: 4

CO I F-Br N C,u, I are also valuable intermediate compounds for producing vat dyes e. y. by condensing them with aminoanthraquinoncs e. g. in the iollowing way: 40.7 parts of the azimid ob tained from Ltolylamino-2-amino-3-broma anthraquinonc (by treating it with nitrous acid) and 22.3 parts of l-aminoanthraquinone are heated to boiling'fm' 2 hours with the addition of parts of sodium acetate and 2 parts of cupric acetate in 400 parts of nitrobenzene. After being cooled a well crystallized substance separates, which is filtered off and washed with alkali and water. The new dyestufi is dissolved in hot solvents ofa high boiling point e. g. nitrobenzene with an ored azimids. Part of the resulting products orange color and is separated therefrom ucts can be condensed withaminoanthra low-coloration. By treatment with sulfonat- 1 parts being by weight2-5 parts of 1paraacid with the addition of 5 parts of sulfuric g t-ion has turned colorless, .The azimid separates insma'll yellow needles]: They arej sulfuric acid and organic solventswi tha proceeds most I solved with a dark blue coloration.

well crystallized by cooling. In concen trated sulfuric acid the" substance is dis- It y-iel ds with alkali hydrosulfite a red-brown Vat,

crystallizing from nitrobenzene in yellow needles, soluble in concentrated sulfuric acid with a ellow coloration; dyeing cotton ff'om the hyd rosulfite vat yellow shades; its sul ,fonic acid dyeing wool yellow shades; yielding by condensation with l-aminoanthraquinone a product which dyes cotton from the hydrosulfite vat scarlet-red shades, substantially as described. 1

from which cotton is dyed in scarlet-red shades. The reaction proceeds most probably in accordance with the following equation rivable from orthodiaminoanthraquinones by treating these compounds with nitrous acid, which are from yellow to blue to green compounds soluble in concentrated sulfuric acid generally with a yellow coloration; being converted into wool dyes by treatment with sulfonating agents, substantially asdescribed. 1

2. The new aziminoanthraquinone having most probably the formula:

In testimony whereof I have-hereunto set my hand in the witnesses.

HERMANN FRIEDMANN. [1.- 8.]

Witnesses DORA NUFER, ALBERT NUFER.

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